


Pick Your Battles

by AnOddSock



Series: Learning the Ropes [1]
Category: Supernatural
Genre: Bottom Castiel (Supernatural), Dildos, Dubious Consent, Handcuffs, Human Castiel, Humiliation, Hurt Castiel, M/M, Mean Dean Winchester, Not Safe Sane and Consensual, Object Penetration, Plot What Plot/Porn Without Plot, Predicament Bondage, Teasing, Under-negotiated Kink, Voyeurism
Language: English
Status: Completed
Published: 2018-11-26
Updated: 2018-11-26
Packaged: 2019-08-29 23:14:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,938
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16753297
Author URL: https://archiveofourown.org/users/AnOddSock/pseuds/AnOddSock
Summary: All Cas wanted to do once he was human was learn to be a hunter. To imitate Sam and Dean and be able to handle situations they way they did, to be as resourceful as they were.There was always something nudging him to do better, be better, learn faster, get to grips with the situation sooner. This time the incentive was just a little more literal, a little more intimate.If he could just stop being distracted by how much everything hurt it would be so much easier.If he could just get out of the damned cuffs everything would be fine.





	Pick Your Battles

**Author's Note:**

> The spirit of Kinktober lives on! I started writing this and didn't plan on it going this way or being so cruel, and then Dean got mean (I suppose he does have the Mark at this point?) and Sam turned out to be a big fat voyeur and I couldn't make them behave so I just went with it.
> 
> Yes the title is a pun.

Struggling didn’t help. In fact it made things worse but he hadn’t fully convinced his limbs to stop jerking around. With his entire weight balanced on the balls of his feet, as he pulled hard on the manacles around his wrists, staying still was the better, less painful option.

Except for his ass. That was hurting no matter what.

More sweat beaded around his forehead and stung as it rolled into his eyes. He blinked rapidly, trying to clear it, needing to see. He had to see, he had to make sure he did this right.

His fingers fumbled, numbed a little from the restricted blood flow. He huffed an annoyed breath. Pain was just sensation ramped up a few extra notches, it wasn’t of consequence, he knew this. It’s just… well it did still hurt.

There were a great many things to get used to without his grace; heat, cold, hunger, longing, needs and wants and necessities. It was a lot for his mind to process, for his consciousness to encompass, even on the good days. Dean was showing him how to use it all to his advantage, make it a driving force to keep going and stay alive. And maybe Cas was just a terrible student, but it always seemed to end up hurting.

He gripped the chain connected to the cuffs to steady his weight and tilted his head further back, groaning low at the extra pressure on his shoulders. Still the light wasn’t good enough and he couldn’t make out what he was supposed to be doing. The lock pick in his right hand was his lifeline, and he held it tight but let himself sag for a moment letting his arms straighten and his knees bend so his body hung lower. Just a few seconds to compose, to settle, to calm.

It pushed the intrusion deeper into his ass and he swallowed thickly. It would’ve felt good, it should, Dean had put it there and he wanted to like it but his body rebelled. It didn't feel right having something inside him that wasn't real, that wasn't welcome. It was nothing like the times Dean had taken him to his bed, this was all degradation and pain.

Not that his cock had got that message.

More than his own discomfort he hated it because every new inch that entered him was a sign he wasn't succeeding and he didn’t want to fail, didn’t want to be useless and worthless and mocked and and and…

His thoughts spiralled and he shuddered.

And then he collected his scattered emotions and was about to try again when Sam walked in.

He wailed in surprise and lost his balance, it jarred his whole body and his breathing came in short sharp bursts while he tried to regain his posture.

Sam looked at him in shock, eyebrows raised and mouth agape while Cas panted and his chest heaved. He slowly pushed his tired legs straight again, back up on his toes where he was closer to his goal and had less plastic widening the rim of his hole.

“How did you get yourself in this position?” Sam asked eventually.

Cas looked down the long suspended line of his torso and the spread of his legs either side the stool between his feet and shuddered again. He was losing focus, and he couldn’t do that.

He shook his head. “Dean,” he croaked, “t-to practice.”

He couldn’t force more words out and looked up willing Sam to understand. Sam who was never supposed to see him like this, Dean had promised.

Dean promised a lot of things.

Sam nodded, appraising, closing the door softly behind him.

“Want me to find the keys?”

Cas went wide eyed, jaw twitching. He clutched his way out a little tighter — a thin metal stick that could so easily have snapped if he was at full strength — and shook his head.

“Got to do it the hard way,” he replied breathlessly.

“Okay.”

He thought Sam would leave, he hoped he would, and hoped he’d forget he ever saw but he just leaned against the wall and folded his arms.

“You…?”

“It’s a good show, I thought I’d make sure you made it all the way to the end.”

Cas’s foot slipped a fraction, and he clenched and cried out, the dildo affixed to the top of the stool spearing him further. He regained his footing on shaking legs. If he slipped down, if he lost energy and let his legs give out he might not get back up and if he didn’t get back up there was no way to tell how long he might dangle from his wrists unable to manipulate the locks. Dean was methodical, immovable, a lesson was a lesson and he wouldn’t be leaving until he learned it.

“Sam, don’t—”

It wasn’t like Sam was really stealing his concentration but it was a good excuse.

“You look so… debauched.”

He moaned in agreement, he knew, he could imagine. Dean had shown him his bound form in a mirror before he’d left Cas alone to get free.

“You must be crazy for him to put up with this.”

“It’s not like that.” Cas replied, dismissive, looking away. He steeled his resolve, gripped the chain with his free hand and hauled himself onto his toes to get a better look.

“Really? What is it like?” Sam asked.

“Just… trying to learn. Got to do better.”

“Mmm, breaking you down bit by bit, so he can build you back the way he wants you. Clever.”

Cas wished Sam would stop talking so he didn't reply, instead twisting his wrists and curling the lock in his fingers, trying desperately to scrape it inside the tiny keyhole. It kept slipping out before he could get the angle right to do anything helpful.

The door creaked open but Cas didn’t falter.

“Oh I see you found our schoolroom for the day.” Dean said as he entered. Cas saw him saunter passed Sam and settle back into his chair.

“Yeah, pretty enticing way to plan a lesson.”

Dean waved his hand dismissively, “Eh, it gets boring once you’ve seen it once or twice. Have to keep upping the stakes to keep it interesting.”

Cas tried to zone them out but it was hard. He got the thin metal rod where it was supposed to go and froze, not even daring to blink.

“How many times have you done this?” Sam asked incredulously.

“This specifically? This is the first time with all these incentives. He’s got to learn the things a hunter should know, though.”

“Couldn’t think of a better way to teach him?”

“Better than this? Come on, as if that were possible. I worked my ass off getting this right. Well… I put his ass on the line, basically the same thing, right?”

Cas flicked his eyes down and saw Sam laugh, shaking his head, as he settled onto the floor next to Dean’s chair.

“It’s not like this is his first time picking a lock I’m not _that_ bad a teacher. But he’s always had comfort and time on his side before, in a real situation he wouldn’t have that luxury.”

Cas moved slowly, hand turning a fraction of a millimetre at a time, trying to find a way to manoeuver the lockpick in the right direction without pulling too quickly or missing the mark altogether.

He didn’t make it and everything slipped, he lolled forward swinging from his arms and the large fake cock bumped his prostate making everything white out. The thing in his ass had shifted against the sweet spot one too many times and the result was getting more and more electric, a live wire of shocks now, intense and overwhelming.

He didn’t know how much longer he could go on for. He rested his head on his up-stretched arm and looked pleadingly at Dean.

“I can’t.”

“Gonna be a long day for you then isn’t it?”

He groaned. Dean’s message was clear, get free or stay put, the outcome was entirely up to him.

Dean gestured with a few quick turns of his hand and nodded encouragingly. “Keep going.”

Cas hung his head and hauled his weight up, stretching to reach the pulled taut chain above his head.

“So… what happens if he drops it?” Sam said quietly.

Everything stopped, thoughts screeched to a halt, and Cas’s mind scattered and rolled away across the floor. He curled his fingers protectively around his only way out.

He hadn’t considered that, hadn’t thought to worry about it.

Dean looked knowingly at Sam and tapped his nose.

“I have to keep some things up my sleeve, but let’s just say he doesn’t want to find out.”

Sam laughed, pressing a hand to his crotch and rubbing through the fabric.

“Bastards,” Cas muttered.

Dean mockingly put a hand to his ear. “What was that?”

“Nothing.”

“Good, because I don’t mind leaving to go find you a gag, if you need it.”

Cas ignored the comment in favour of returning to his work. There were some things he just wasn’t willing to give up on, but he knew when he was in a losing battle and mouthing off wouldn’t get him anywhere good.

They sat and watched him in silence for a while as he methodically began again, trying valiantly to ignore the way he was shaking. He watched his hand move, willing with everything he had to find the rhythm, the pattern, to imitate the way he’d seen Dean do this.

“You know, we’ll treat you real nice once you get free,” Dean said, low, grating.

“Oh yeah? Does he get rewarded?” Sam asked.

Cas whined. Rewards. Enticements. Incentives. His life seemed to be a series of interlocking puzzle pieces that he couldn’t see the picture of.

He shook his head briefly, dispelling the thoughts. Don’t think, just _do._

“He gets whatever feels appropriate. If his performance isn't sufficient we go again.”

He heard Sam moan wantonly, and took a shaky breath, that wasn’t going to happen. He wouldn't let it, he'd be good enough.

“You’ve got this though haven’t you?” Dean asked him. “You’re going to make us all proud, right? No disappointments, no let downs?”

Cas flicked his eyes down briefly and saw the scrutiny on Dean’s face.

“Trying,” he bit out.

“Oh, well, as long as you’re _trying_.” Dean said with an exaggerated roll of his eyes.

Cas had no idea how long he’d been held in place here, somehow under Dean’s tutelage it was easy to lose track of time. He only knew when his body was reaching its limit and he felt it approaching like a rumble under his feet. He’d sunk lower now, more of his feet braced either side of the tool of his discomfort. If it weren’t there he could close his legs and stand taller more easily, if it weren’t there he wouldn’t be fucking himself raw on a dildo he didn’t care to remember the size of.

He had to do this now, right now, before his legs lost all strength and his chances dipped even lower. He grit his teeth, breathed long, and stopped thinking, only feeling for the twang and jolt through the touch of his fingers. He finally snagged the mechanism and moved with the correct degree of force, holding his breath to keep everything steady.

When the metal clicked, and the first cuff sprang open freeing his wrist he cried out in delight.

And then he slipped. And gasped.

And flailed.

The chain pulled through the hook fastening him to the ceiling and without its helping balance to steady with he couldn’t stay up on his toes.

He sank down, clammy feet sliding on the floor as gravity pulled him down. His core muscles tightened but it did nothing to help, and his hole clenched as it sucked the ribbed plastic inside inch by inch in quick succession.

He yelled high and long as his ass made contact with the seat of the stool, every long inch of the dildo finally buried inside him.

He panted hard, aware of his still manacled hand swinging, and the other clutching the seat. He tried to heave himself off, to stand and _get it out_. But he was too exhausted and it hurt too much.

Dean grinned at him, a cat-like smile in the darkened room, and Sam was agape, face eager and open.

He realised then that it had always been going to happen. There was no way out of his predicament that didn’t end with him stuffed full of plastic, impaled when he thought he was about to get free.

“Dean.” he choked.

It hurt. It was humiliating. His cock was still full, erect and blood red, and he moved to cover it. He didn't feel aroused, but he’d been tormented with a slow increase in stimulation to his ass for every second of time he’d been suspended. His newly human body responded to everything with such fervour that he couldn’t make it stop.

 _“Dean.”_ He said again, pleading, as his feet scrabbled at the floor.

“Hush, you’re fine. It’s not a problem.”

Dean stood from his chair and stalked towards him. He caught up Cas’s hands and kissed each of them.

“Look at you, learning. Making me so proud.”

He cocked his head at Sam, beckoning him over. Cas turned begging eyes to Dean, breath stuttering between heartbeats.

“Want to have a little play with Sam?”

Cas shifted his hips, trying to rise, and Dean rushed behind him dragging his arms behind and down. Cas screamed as he was forced to arch his back and the fake cock in his ass pressed harshly up and forwards.

He felt the rough slide of metal around his recently free wrist and tried to twist away only to be pulled short.

“This was not the deal!” he accused.

He’d got down hadn’t he? It wasn’t an elegant way to phrase his displeasure but Dean knew what he meant.

His arms were locked in place to the leg of the stool and he heard the clank of the chain as he tried to move. He looked down to where Sam was perched by his feet looking eagerly at Cas’s cock. It had wilted a little at the new position, the new pain in his gut.

He was still tightly clutching the lock pick and Dean wrenched it out of his closed fist.

He sobbed, half a growl, half desperation.

“Give it back.”

“You can have it back,” Dean said, twirling it around his fingers. “Or… you can have Sam touch you.”

He reached out and picked up Sam’s hand, moving it forward until Sam’s knuckles brushed the underside of the sensitive head of Cas's cock.

Cas bowed backwards at the touch, arms pulling taut, the hard press of the toy in his ass poking outwards through the stretched skin of his stomach.

Sam's touch sent wild, singing energy coursing through his blood stream, making it hard to think. Making it hard not to cry.

“No, no, Dean I did your lesson, I won.”

“Lesson two: tough choices, which one are you going to make?”

He looked wildly between them, both offering different kinds of relief. He didn’t know which one he wanted. His mind was awash with so many differing feelings, physical and emotional, sensation and pain and need and desire.

“Please,” he begged, “help me.”

Sam leaned in and kissed his stomach and his thigh, curling a hand around his calf. His skin prickled at the contact, nerves alight, his whole body aware and alert. Had he ever felt this alive before?

“What kind of help do you want?” Sam asked, rubbing his thumb in lazy circles. Sam seemed sincere, he seemed eager and caring.

His body was urgently telling him to pick something, do _something_. He was wrecked. This new position put strain on so many different parts of his body, he couldn’t even lean forward. His legs out to the side, his ass squashed down around the thing stuffed inside him. His arms pinned behind and his abdomen aching, his ass throbbing in time with his heartbeat.

As an angel he would never have deigned to be debased in this way, utterly spent and begging. But without his grace he was at the mercy of the world, and sometimes they were his whole world.

He closed his eyes, willing a decision to take shape.

Dean pressed close, until their foreheads were touching, and there were hands gripping his curving waist. Cas longed for contact, and whimpered, despite his best efforts.

“We’ll leave you to think a while, see if that clears your head.” Dean whispered.

His eyes flew open to the sight of them turning to walk out the door, to leave him shame faced and desperate.

“Wait!” he cried. He was a soldier he was a tactician, he should be able to match Dean in a battle of wits no matter how tired, dirty, and confused he might be.

“What do I have to do to get both?” he asked, pleading. Breathless need making the words thin and reedy, his whole body yearning for attention.

“Now, _there’s_ the right question.” Dean leaned over and kissed him.

Cas let out a surprised gasp at the press of lips and tongue, warmth and want making themselves known. Dean bit at his mouth and tugged on his hair a little before smoothing it down and pulling away, releasing Cas’s lip from between his teeth with a grunt of pleasure. “I thought you’d never ask.”

**Author's Note:**

> Dean, don't tease the ex-angel it's not polite.
> 
> (I hope it goes without saying but... don't tie someone up and leave them in real life, that's the opposite of fun and kinky.)
> 
> Leave me a note of your presence if you liked it, let's enjoy the hurt Cas together!


End file.
